Thionyl Chloride → HCID 10321793, compound

HRID 1379119Notes

Reaction equation

HRID 1379119 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1.[C:16]([C:18]1[CH:34]=[CH:33][C:21]([C:22]([N:24]2[CH2:31][CH2:30][CH2:29][C@@:25]2([CH3:32])[C:26](O)=[O:27])=[O:23])=[CH:20][CH:19]=1)#[N:17].S(Cl)(Cl)=O>>[C:16]([C:18]1[CH:34]=[CH:33][C:21]([C:22]([N:24]2[CH2:31][CH2:30][CH2:29][C@@:25]2([CH3:32])[C:26]([N:1]2[CH2:2][CH2:3][CH:4]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]2)=[O:27])=[O:23])=[CH:20][CH:19]=1)#[N:17]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetateHCID 10445222HCID 10445222, compound

Product 1

HCID 10321793HCID 10321793, compound

Procedure

By reacting 1.67 g of t-butyl 4-piperidinyloxyacetate with 0.8 g of the acid chloride of 1-(p-cyanobenzoyl)-2-methyl-L-proline (obtained by treating the product of the previous step with thionyl chloride) there is obtained 0.89 g of t-butyl [[1-[1-(p-cyanobenzoyl)-2-methyl-L-prolyl]-4-piperidinyl]oxy]acetate. M.p. 180°-182° C. (ethyl acetate).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-2ef39c8c0e9f43748c51b8569ea267d1
Source dataset
uspto-grants-1997_09
Patent number
US05670515

Reaction notes

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